Sodium Iodide → HCID 18961583, compound

HRID 1707545Notes

Reaction equation

HRID 1707545 reaction equation
ClC[CH2:3][C:4]([CH3:9])([CH3:8])[C:5]([O-:7])=[O:6].[C:10]([NH:13][C:14]1[C:15]([I:30])=[C:16]([N:25]([C:27](=[O:29])[CH3:28])[CH3:26])[C:17]([I:24])=[C:18]([C:21]([O-:23])=[O:22])[C:19]=1[I:20])(=[O:12])[CH3:11].[K+].[I-].[Na+].[CH3:34]N(C)C=O>>[C:10]([NH:13][C:14]1[C:15]([I:30])=[C:16]([N:25]([C:27](=[O:29])[CH3:28])[CH3:26])[C:17]([I:24])=[C:18]([C:21]([O:23][CH2:34][O:7][C:5](=[O:6])[C:4]([CH3:9])([CH3:8])[CH3:3])=[O:22])[C:19]=1[I:20])(=[O:12])[CH3:11]

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 6228Dimethylformamide2×HCID 217530474-Chloro-2,2-dimethylbutanoateHCID 23717801potassium 5-(N-acetylamino)3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Product 1

HCID 18961583HCID 18961583, compound

Procedure

Chloromethylpivalate (12.0 ml., 82.6 mmol) in dry DMF (130 ml) is added dropwise during 20 minutes at 50° C. to a solution of potassium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate (50.0 g, 75.0 mmol) and sodium iodide (600 mg, 4.0 mmol) in dry dimethylformamide (DMF) (750 ml). The precipitate is removed by filtration after stirring for 4 hours and the solvent removed at reduced pressure. The residue is dissolved in chloroform (400 ml) and washed four times with a saturated sodium hydrogen carbonate solution. After drying with magnesium sulfate the solvent is removed at reduced pressure and the residue recrystallized from acetone to give the title compound: 26.6 g (53%); m.p. 232°-234° C. 1H-N.M.R. (CDCl3): delta=1.26 (s, C(CH3)3); 1.82 (s, N(CH3)COCH3); 2.22 (s, NCOCH3); 3.08 (s, NCH3); 6.02 (s, CH2); 8.15 ppm (s, NH).

Workup

  1. customThe precipitate is removed by filtration
  2. customthe solvent removed at reduced pressure
  3. dissolutionThe residue is dissolved in chloroform (400 ml)
  4. washwashed four times with a saturated sodium hydrogen carbonate solution
  5. dry with materialAfter drying with magnesium sulfate the solvent
  6. customis removed at reduced pressure
  7. customthe residue recrystallized from acetone

Sources & evidence

ORD record
ord-d6c2e0ca47bf4c7f8d7d8db9b4c13231
Source dataset
uspto-grants-1994_10
Patent number
US05354549

Reaction notes

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